Holiday rentals with a pool in Middlesex County

4.97 out of 5 average rating, 334 reviews

Flat in Waltham

Cozy Private Studio Unit w/ Laundry and Parking!

Almost every guest describes my place as cozy, which was the feeling I was going for when I designed the space! You'll love this good sized 300 sq. ft PRIVATE 1 bedroom studio. This unit has its own entrance w/ punch code door, full bathroom, large walk-in closet, mini fridge, freezer and microwave. It has one parking spot in the driveway and a washer /dryer. The backyard is shared but the unit has a private patio. Rental is attached to a single family home. (Please note: No full kitchen)

4.96 out of 5 average rating, 101 reviews

Home in Worcester

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

★ "Tania’s place was much more then a place….it was a full on fabulous experience." ☞ Courtyard w. lounge + garden ☞ Pool! ☞ Patio w/ Zen fire table* ☞ Natural gas + charcoal grills ☞ Reverse osmosis water filter ☞ 66” smart TV projector ☞ Air filter + purifier: whole house ☞ Central air conditioning ☞ Apple Home pod mini's ☞ Indoor gas fireplace ☞ 300+ Mbps WiFi For non-smokers. No smoking inside or outside. 8 mins → DT Worcester (shops, dining) 17 mins → Worcester Regional Airport [ORH]✈

4.95 out of 5 average rating, 155 reviews

Home in Hopkinton

Hopkinton Mass 3+ Bedrooms - Great location!

This my home in which I am now an "empty-nester". I have 3 bedrooms available, each with a Queen bed, plus a room over the garage with 2 futons and a mattress. NOTE: I live here and will be home during your stay. You'll have access to a private bathroom and the rest of the house: kitchen, dining room, living room, etc. NO pets allowed My place is close to Boston, Worcester, Providence, state parks, etc. Good for singles, couples, business travelers and families. Great pool and hot tub!

5 out of 5 average rating, 28 reviews

Guest house in Maynard

Cute mill house: 3BR•Wood stove *Brkfst included*

Welcome to the most walkable town in Metro Boston, w/ movie theater, live performance venue, beer garden, galleries, shops, & 17 restaurants 1/2mi from our front door. Our 1910 mill town company house is a little oasis. This is a two-family house; two separate private residences side-by-side. My family occupies the other side. Between house & garage, the outside dining area and fire pit are for your private use. Beyond the garage, we invite you to share our backyard w/ pool and badminton.

5 out of 5 average rating, 24 reviews

Flat in Fitchburg

Relaxing Poolside Getaway

Welcome to our charming 1-bed, 1-bath side-by-side unit, a perfect paradise with poolside access available during the warmer months! My husband and I, along with our cat, Mia, live in the main house. Enjoy the TVs in both the living room and bedroom, each offering streaming options, along with a fully equipped kitchen. The futon converts into a full-size bed for additional guests. It’s a great place to unwind, whether indoors or relaxing in the backyard setup. We look forward to hosting you!

4.96 out of 5 average rating, 51 reviews

Flat in Somerville

Lux 2BR Apt w/ Pool and Gym

Welcome to your perfect getaway! Our space combines the comforts of home with luxurious amenities to make your stay truly special. Highlights: • Conveniently close to Downtown Boston • Meticulously deep-cleaned before every stay • Complimentary gourmet coffee, fresh linens, and premium bathroom essentials • 24/7 access to a state-of-the-art fitness center • Modern yoga studio and high-tech training equipment • Experience the charm of Somerville while enjoying hotel-quality amenities at home

4.97 out of 5 average rating, 95 reviews

Home in Weston

Spacious vacation unit in premium suburban town

Weston is one of Boston area's most desirable towns. <30 min to downtown Boston with a lot of open space. Centrally located with easy access to highways, train stations, etc. Next to a park with hiking trails, this is a secondary unit (Duplex units) with its own separate entry/exit. 3 bedrooms (one on lower level, two on 2nd level), kitchen, 2 baths (both on lower level). ~2K Sqft of space. There are chickens in the backyard...the host can provide some fresh eggs too if desired.

4.9 out of 5 average rating, 104 reviews

Flat in Malden

Luxe Serene 1BR 15 min from Boston with Gym & More

You will love this beautifully designed 1 Bedroom 1 Bath luxury unit that is in a central location between many great cities! You will be staying in a gorgeous private community with a gym, pool table, dog park, kids playground, tennis court, and tons of outdoor space. Have peace of mind knowing you’re in a safe space. Our luxury suite has a Queen Medium Firm bed along with a Queen Air Mattress for any additional guests. Check out more of our amenity spaces below!

5 out of 5 average rating, 83 reviews

Flat in Groton

Farmhouse Guest Apartment

Welcome to our quiet private guest apartment! Our property, is surrounded by fields, woods, gardens, and a pond. You will enter through a shared entrance & stairway in our home, but have an entire 725 sq. ft. guest apartment all to yourself that includes a living room, full kitchen, bathroom, and large bedroom with a desk. It has ample light with views of fields, stone walls, Christmas trees and our barn. Out back we have a pool, BBQ, table & chairs you may use.

4.96 out of 5 average rating, 121 reviews

Flat in Holliston

Lake Link

Beautiful fully stocked 2 BR apartment located in Holliston Historic District. Top of the line swimming pool with waterfall and hottub (May 31-Sep 30). Full kitchen, full bath, washer/dryer, central heat and AC, fireplace, wireless internet, Cable TV with almost all premium channels available, private driveway and entrance. Sorry, but no pets allowed. Note: COVID19- We require all eligible guests to be vaccinated or have 72 hr negative test.

4.94 out of 5 average rating, 157 reviews

Home in North Andover

Nana-tucket Inn

Charming historic town, home of Brooks School and Phillips Academy, 30 minutes to Boston and Seacoast. Families will enjoy our children’s park and town park, just a short walk from property. Enjoy pastural views while relaxing poolside (availability May 1 - Oct 1)in a quiet & private backyard setting. Hot tub is also open May 1 til Nov 1. Seven minutes to commuter rail for those who desire traveling into Boston, no hassle!

4.8 out of 5 average rating, 15 reviews

Flat in Boston

The Watson-Luxe Boston Studio

Experience Boston in this beautiful studio unit near the heart of the city! Just a 5 min walk from the T and close to Boston College/Harvard, you can tastefully engage with all of Boston. Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> Fully Stocked Kitchen -> Washer & Dryer -> 1 Queen Bed Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

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Popular amenities for Middlesex County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 19 reviews

Home in Newton

Villa with private Pool in Boston's Elite Enclave

JonRating, 5 stars2 weeks ago

Great option when staying in Newton and right down the street from an incredible entrance to a hiking trail. Serge was a great host and kept us informed the entire trip.

4.94 out of 5 average rating, 34 reviews

Home in Arlington

Beautiful Spacious 4BRM House!

NicholasRating, 5 stars1 week ago

I loved everything Maxine said and how she helped navigate around every even in the house, everything was so clean, very quite place good for professional working, everything was just beyond, amazing & lovely place you feel right at home with so much space to move around the house. Being free having your privacy. Thank you Maxine 🙏👏🏽

4.95 out of 5 average rating, 44 reviews

Home in Norwood

the house of id; vintage shop, accessible space

JasonRating, 5 stars6 days ago

Super fun and eclectic house! What really made the stay were the owners, they are thoughtful and very responsive, they clearly care a lot about their guests!

Home in Worcester

4.78 out of 5 average rating, 32 reviews

Beautiful & Historic Cottage, Steps to Elm Park

AmyRating, 5 stars1 month ago

location was easy to find in a nice residential area just outside of the city, very clean, owner responded quickly to messages

4.88 out of 5 average rating, 25 reviews

Home in Canton

Hidden Gem near Boston w/ Private lake access

RachaelRating, 5 stars1 month ago

Absolutely incredible stay. The host was very helpful. The house is absolutely beautiful, and the lake is stunning. The basement was so so fun- darts, ping pong, billiards, and more games. We miss the house already!

4.9 out of 5 average rating, 50 reviews

Home in Waltham

Quiet/Private Neighborhood

ElmerRating, 5 stars1 week ago

Hands down one of the best Airbnbs my family and I have stayed in! We didn't want to leave this place. To top it off, Michelle is a great host. 5/5 rating for sure!

4.92 out of 5 average rating, 12 reviews

Home in North Andover

Peaceful New England Retreat Close to It All

AmyRating, 5 stars8 months ago

The home was so lovely and comfortable - perfect for our family. It had so many amenities, and comfortable sleeping spaces. It looks exactly like the pictures. We will definitely return!